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Tortola

$280+ Cheap flights from Chicago (CHI) to Tortola

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EIS
May 18 — May 251
Mon 5/18
Mon 5/25
1 adult, Economy
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Cheap flight deals from Chicago to Tortola

Cheapest flights from Chicago to Tortola
Explore the most affordable flight options available from Chicago to Tortola. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 18, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/12:09 pm
ORD
-
EIS
2 stops19h 46m
Multiple Airlines
Mon 5/44:00 pm
EIS
-
ORD
1 stop24h 11m
Multiple Airlines
Deal found 4/17$544
This Kiwi.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/107:30 am
ORD
-
EIS
2 stops26h 25m
Multiple Airlines
Sun 5/249:00 am
EIS
-
ORD
1 stop7h 49m
Multiple Airlines
Deal found 4/16$560
This Kiwi.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/192:00 pm
ORD
-
EIS
2 stops19h 55m
Multiple Airlines
Sat 4/259:00 am
EIS
-
ORD
1 stop12h 49m
Multiple Airlines
Deal found 4/16$576
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1210:27 am
ORD
-
EIS
2 stops23h 28m
Multiple Airlines
Wed 8/199:00 am
EIS
-
ORD
1 stop13h 04m
Multiple Airlines
Deal found 4/17$581
This Kiwi.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/242:20 pm
ORD
-
EIS
2 stops26h 50m
Multiple Airlines
Sat 5/29:00 am
EIS
-
ORD
1 stop12h 49m
Multiple Airlines
Deal found 4/16$582
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/612:33 am
ORD
-
EIS
1 stop9h 22m
Multiple Airlines
Mon 6/154:00 pm
EIS
-
ORD
2 stops45h 43m
Multiple Airlines
Deal found 4/14$585
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/214:44 pm
ORD
-
EIS
1 stop24h 26m
Multiple Airlines
Thu 5/284:00 pm
EIS
-
ORD
2 stops45h 37m
Multiple Airlines
Deal found 4/17$588
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/612:33 am
ORD
-
EIS
1 stop9h 22m
Multiple Airlines
Tue 6/164:00 pm
EIS
-
ORD
1 stop8h 29m
Multiple Airlines
Deal found 4/14$596
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/612:33 am
ORD
-
EIS
1 stop9h 22m
Multiple Airlines
Wed 6/179:00 am
EIS
-
ORD
1 stop7h 11m
Multiple Airlines
Deal found 4/14$602
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/214:44 pm
ORD
-
EIS
1 stop24h 26m
Multiple Airlines
Wed 5/274:00 pm
EIS
-
ORD
1 stop24h 49m
Multiple Airlines
Deal found 4/17$605

Find flight deals from Chicago to Tortola

Keep the following information in mind while searching for Chicago to Tortola flight deals. Data was last updated April 18, 2026.

Round-trip from

$544
(Kiwi.com)

One-way from

$280
(Kiwi.com)
From Chicago (CHI) to Tortola
Search Deals
One-way flight from Chicago (CHI) to Tortola
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Tortola that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 18, 2026.
Use the filters below to find and compare flights from Chicago to Tortola that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sun 6/7

7:52 pm-10:55 am

2 stops14h 03m

Road Town Beef Island

Tue 6/16

4:00 pm-11:29 pm

1 stop8h 29m

$688

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Thu 6/25

8:48 am-9:58 pm

2 stops12h 10m

Road Town Beef Island

Thu 7/2

2:23 pm-11:59 pm

2 stops10h 36m

$793

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Wed 6/24

5:00 am-9:58 pm

1 stop15h 58m

Road Town Beef Island

Wed 7/1

12:22 pm-12:19 am

1 stop12h 57m

$793

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Wed 5/20

5:00 am-9:10 pm

1 stop15h 10m

Road Town Beef Island

Wed 5/27

12:22 pm-12:24 am

1 stop13h 02m

$903
Cheapest one-way
Quickest one-way

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Thu 5/21

10:49 am-6:10 pm

2 stops30h 21m

$316

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/14

Sorted by cheapest first

Best time to book a flight from Chicago to Tortola

Have a flexible travel schedule? Discover the best time to fly to Tortola from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Tortola
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Tortola

Get insights into the airlines that provide service to Tortola. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Tortola. Reviews last updated April 18, 2026.
Read through reviews of airlines operating flights from Chicago to Tortola, such as American Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.1
Good
11,604 reviews

Boarding

7.5

Entertainment

6.9

Crew

7.9

Comfort

7.2

Food

6.4

Overall

7.1

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.
American Airlines
7.1
Good
11,604 reviews
American Airlines
7.1
Good
11,604 reviews

Boarding

7.5

Entertainment

6.9

Crew

7.9

Comfort

7.2

Food

6.4

Overall

7.1

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Tortola. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Tortola?

    Airlines like American Airlines fly from Chicago to Tortola in about 12h 10m. The time it takes to get you to your destination can typically vary by up to . The distance between Chicago and Tortola is about 2126 mi.

  • Can I find deals for flights from Chicago to Tortola that include hotel bookings?

    Yes. In addition to deals on Chicago to Tortola flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Tortola?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Tortola.

  • Can I find deals for business class flights from Chicago to Tortola?

    Yes. Cheapflights offers flight deals from Chicago to Tortola by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Complete your trip

Complete your trip to Tortola by adding a car rental and/or hotel reservation to your travel itinerary.
Road Town Beef Island Airport car rentals

Top airline flying from Chicago to Tortola

Discover the top airline that operate flights from Chicago to Tortola. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$693Average$918FlexibilityNo cancel feeOn-time71%

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